EP0901472B1 - Mercapto-imidazolyl-derivate und ihre verwendung als mikrobizide - Google Patents

Mercapto-imidazolyl-derivate und ihre verwendung als mikrobizide Download PDF

Info

Publication number
EP0901472B1
EP0901472B1 EP97923034A EP97923034A EP0901472B1 EP 0901472 B1 EP0901472 B1 EP 0901472B1 EP 97923034 A EP97923034 A EP 97923034A EP 97923034 A EP97923034 A EP 97923034A EP 0901472 B1 EP0901472 B1 EP 0901472B1
Authority
EP
European Patent Office
Prior art keywords
formula
mercapto
methyl
ethyl
wie
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP97923034A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0901472A1 (de
Inventor
Manfred Jautelat
Ralf Tiemann
Stefan Dutzmann
Klaus Stenzel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP0901472A1 publication Critical patent/EP0901472A1/de
Application granted granted Critical
Publication of EP0901472B1 publication Critical patent/EP0901472B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • the present invention relates to new mercapto-imidazolyl derivatives, several Process for their preparation and their use as microbicides.
  • EP-A 0 297 345 and EP-A 0 052 424 show that certain triazoles and imidazoles can be used as fungicides. However, the compounds listed do not contain a mercapto group on Azole ring.
  • EP-A 0 251 086 relates to triazole derivatives having fungicidal activity, in where the heterocycle is substituted by a mercapto residue. Appropriate Imidazole derivatives are not mentioned.
  • the substances according to the invention have better microbicidal properties Efficacy as the most constitutionally similar, known compounds same direction of action.
  • the mercapto-imidazolyl derivatives of the formula (I) in which R represents hydrogen can be in the "mercapto” form of the formula or in the tautomeric "thiono” form of the formula available. For the sake of simplicity, only the “Mercapto” form is listed.
  • Imidazoles of the formula (II) are known or can be prepared according to known ones Produce methods (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0 061 835, EP-A 0 297 345, EP-A 0 094 564, EP-A 0 196 038, EP-A 0 267 778, EP-A 0 378 953, EP-A 0 044 605, EP-A 0 069 442, EP-A 0 055 833, EP-A 0 301 393, DE-A 2 324 010, DE-A 2 737 489, DE-A 2 551 560, EP-A 0 065 485, DE-A 2 735 872, EP-A 0 234 242, DE-A 2 201 063, EP-A 0 145 294 and DE-A 3 721 786).
  • Produce methods cf. EP-A 0 015 756, EP
  • the bases used in carrying out the first stage of the invention Process (variant a), all strong alkali metal bases customary for such reactions into consideration.
  • Solvents are considered as diluents.
  • Ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane, further liquid ammonia or strongly polar solvents, such as dimethyl sulfoxide.
  • Sulfur is preferably used in the form of powder.
  • Procedure (variant a) Water, optionally in the presence of an acid.
  • organic acids In All inorganic or customary for such reactions come here question organic acids.
  • Acetic acid, dilute, can preferably be used Sulfuric acid and dilute hydrochloric acid.
  • hydrolysis is also possible perform with aqueous ammonium chloride solution.
  • reaction temperatures can be carried out when carrying out the first stage of inventive method (variant a), within a certain range can be varied. In general, temperatures between -70 ° C and + 20 ° C, preferably between -70 ° C and 0 ° C.
  • Variant (a) is generally 2 to 1 mol of imidazole of the formula (II) 3 equivalents, preferably 2.0 to 2.5 equivalents, of strong base and then an equivalent amount or an excess of sulfur.
  • the reaction can be carried out under a protective gas atmosphere, e.g. under nitrogen or Argon.
  • the processing takes place according to usual methods. In general, the procedure is that the reaction mixture with a Extracted water little soluble organic solvent, the combined organic Phases dry and concentrate and the remaining residue if necessary purified by recrystallization and / or chromatography.
  • Variant (b) all come as diluents for such reactions usual, high-boiling organic solvents into consideration.
  • Amides such as dimethylformamide and dimethylacetamide can also be used heterocyclic compounds, such as N-methyl-pyrrolidone, and also ethers, such as Diphenyl ether.
  • Sulfur is also used in the implementation of the first stage of the invention
  • Process according to variant (b) is generally used in the form of powder. After the reaction, treatment with water, if appropriate, and optionally with acid. This is carried out as the hydrolysis when carrying out the first stage of the invention Procedure according to variant (a).
  • reaction temperatures can also be carried out when the first stage of the inventive method according to variant (b) within a larger range can be varied. Generally one works at temperatures between 150 ° C and 300 ° C, preferably between 180 ° C and 250 ° C.
  • Variant (b) is generally 1 to 1 mol of imidazole of the formula (II) 5 moles, preferably 1.5 to 3 moles of sulfur.
  • the processing takes place according to usual methods. In general, the procedure is such that the reaction mixture extracted with an organic solvent which is only slightly soluble in water, the combined organic phases dry and concentrate and the remaining Residue, if necessary, by customary methods, such as recrystallization or chromatography, freed of any contaminants.
  • Alkaline earth metal or alkali metal hydroxides such as Sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
  • Alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, Sodium bicarbonate, alkali or alkaline earth metal acetates such as Sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, Triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBU diazabicyclonones
  • DBU diazabicycloundecene
  • the inventive method all inert for such reactions organic solvents.
  • Ethers such as Diethyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, also nitriles, such as acetonitrile, and also strongly polar Solvents such as dimethyl sulfoxide or dimethylformamide.
  • reaction temperatures can be carried out in the second stage of the The inventive method can be varied within a wide range. In general, temperatures between 0 ° C and 120 ° C. preferably between 20 ° C and 100 ° C.
  • 1 mol of mercapto-imidazolyl derivative of the formula (Ia) is generally 1 up to 2 moles of halogen compound of formula (III) and an equivalent amount or an excess of acid binder.
  • the processing takes place after usual methods. In general, the procedure is such that the reaction mixture with an aqueous base and an organic which is not very miscible with water Solvent added, the organic phase separated, dried and concentrated.
  • the the product obtained can optionally be processed by customary methods, e.g. through recrystallization, to be freed from impurities still present.
  • the active compounds according to the invention have a strong microbicidal action and can be used to combat unwanted microorganisms such as fungi and Bacteria can be used in crop protection and material protection.
  • Fungicides are used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes. Basidiomycetes or Deuteromycetes.
  • Bactericidal agents are used in plant protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae or Streptomycetaceae.
  • the active compounds according to the invention are particularly suitable for combating Pyricularia oryzae and Pellicularia sasakii on rice and for combating Cereal diseases such as Pseudocercosporella, Erysiphe and Fusarium species.
  • the substances according to the invention are very good against Venturia and Use Sphaerotheca. They also have a very good in vitro Effect.
  • the substances according to the invention can be used to protect technical ones Materials against infestation and destruction by unwanted microorganisms deploy.
  • technical materials include non-living ones Understand materials prepared for use in engineering have been.
  • technical materials can be produced by the invention Active ingredients protected against microbial change or destruction should be, adhesives, glues, paper and cardboard, textiles, leather, wood. Paints and plastic articles, cooling lubricants and other materials that can be attacked by microorganisms or decomposed.
  • As part of the materials to be protected are also parts of production facilities, for example Cooling water circuits, called by multiplication of microorganisms can be affected.
  • technical materials are preferably adhesives, glues, papers and Cartons, leather, wood, paints, coolants and heat transfer fluids called, particularly preferably wood.
  • the agents according to the invention preferably act Active substances against fungi, in particular mold, wood-staining and wood-destroying Fungi (Basidiomycetes) and against mucous organisms and algae.
  • the active ingredients can depend on their respective physical and / or chemical properties can be converted into customary formulations. such as solutions, emulsions, suspensions, powders, foams, pastes, granules. Aerosols, very fine encapsulations in polymeric substances and in enveloping masses for Seeds, as well as ULV cold and warm mist formulations.
  • formulations are made in a known manner, e.g. by mixing of the active ingredients with extenders, i.e. liquid solvents, under Pressurized liquefied gases and / or solid carriers. possibly using surface-active agents, ie emulsifiers and / or Dispersing agents and / or foaming agents.
  • extenders i.e. liquid solvents
  • surface-active agents ie emulsifiers and / or Dispersing agents and / or foaming agents.
  • organic solvents as Auxiliary solvents can be used.
  • liquid solvents come in essential in question: aromatics, such as xylene, toluene, or alkylnaphthalenes.
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone. Methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; with liquefied gaseous Extenders or carriers are meant such liquids. which are gaseous at normal temperature and pressure, e.g.
  • Aerosol propellants such as butane, propane, nitrogen and carbon dioxide; as fixed Carriers are possible: e.g. natural stone powder. like kaolins. Clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic stone powder, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble.
  • non-ionic and anionic emulsifiers such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl ether, Alkyl sulfonates, alkyl sul
  • Adhesives such as carboxymethylcellulose, natural, can be used in the formulations and synthetic powdery, granular or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used in crop protection as such or in their formulations also in a mixture with known ones Fungicides, bactericides, acaricides, nematicides or insecticides are used e.g. to broaden the spectrum of activity or develop resistance submissions. In many cases you get synergistic effects i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • the following substances can be used as mixing partners.
  • Probenazole prochloraz, procymidone, propamocarb, propiconazole, propineb.
  • Pyrazophos Pyrifenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and sulfur preparations, Tebuconazole, tecloftalam, technazen, tetraconazole, thiabendazole, thicyofen.
  • Thiophanat-methyl Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon.
  • Triadimenol triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin. triticonazole, Validamycin A, vinclozolin, Zineb, ziram.
  • Azinphos M Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinothrinhrhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhr
  • a mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.
  • the active substances can be used as such, in the form of their formulations or in the form thereof prepared application forms such as ready-to-use solutions, emulsifiable concentrates, Emulsions, foams, suspensions, wettable powders, pastes, soluble powders, Dusts and granules can be used.
  • the application happens in usual way, e.g. by pouring, spraying, spraying, scattering, dusting, Foaming, brushing, etc.
  • the active ingredients can be used according to the ultra-low-volume method or to prepare the active ingredient or inject the active ingredient into the soil yourself. It can also be the seed of the plants are treated.
  • the active ingredient concentrations can be in the application forms can be varied in a larger area: generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • amounts of active ingredient are generally from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g.
  • active ingredient concentrations are from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight, is required at the site of action.
  • the means used to protect technical materials contain the Active ingredients in general in an amount of 1 to 95%, preferably from 10 to 75%.
  • the application concentrations of the active compounds according to the invention are directed according to the type and the occurrence of the microorganisms to be controlled and according to the composition of the material to be protected.
  • the optimal amount to use can be determined by test series.
  • the application concentrations are in the range of 0.001 to 5% by weight, preferably of 0.05 to 1.0% by weight based on the material to be protected.
  • Active ingredients to be used or the agents, concentrates that can be produced therefrom or more generally wording can be increased if necessary further antimicrobial compounds, fungicides, bactericides, Herbicides, insecticides or other active substances to enlarge the spectrum of activity or achieving special effects such as the additional protection from Insects can be added. These mixtures can have a broader spectrum of activity possess than the compounds of the invention.
  • the plants are grown in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of about 80% set up the development of mildew pustules.
  • Evaluation is carried out 10 days after the inoculation. 0% means a Efficiency that corresponds to that of the control, while 100% means. that no infestation is observed.
  • the plants are then grown in a greenhouse at 21 ° C and a relative Air humidity of approx. 90% set up.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP97923034A 1996-05-21 1997-05-09 Mercapto-imidazolyl-derivate und ihre verwendung als mikrobizide Expired - Lifetime EP0901472B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19620408A DE19620408A1 (de) 1996-05-21 1996-05-21 Mercapto-imidazolyl-Derivate
DE19620408 1996-05-21
PCT/EP1997/002374 WO1997044323A1 (de) 1996-05-21 1997-05-09 Mercapto-imidazolyl-derivate und ihre verwendung als mikrobizide

Publications (2)

Publication Number Publication Date
EP0901472A1 EP0901472A1 (de) 1999-03-17
EP0901472B1 true EP0901472B1 (de) 2003-04-09

Family

ID=7794886

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97923034A Expired - Lifetime EP0901472B1 (de) 1996-05-21 1997-05-09 Mercapto-imidazolyl-derivate und ihre verwendung als mikrobizide

Country Status (8)

Country Link
US (1) US6114539A (ja)
EP (1) EP0901472B1 (ja)
JP (1) JP2000511164A (ja)
CN (1) CN1226235A (ja)
AU (1) AU2894997A (ja)
BR (1) BR9709019A (ja)
DE (2) DE19620408A1 (ja)
WO (1) WO1997044323A1 (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6620939B2 (en) 2001-09-18 2003-09-16 General Electric Company Method for producing bisphenol catalysts and bisphenols
US7112702B2 (en) * 2002-12-12 2006-09-26 General Electric Company Process for the synthesis of bisphenol
WO2013047308A1 (ja) * 2011-09-27 2013-04-04 株式会社クレハ アゾール誘導体、農園芸用薬剤および工業用材料保護剤、植物病害防除方法ならびに種子
KR20140098145A (ko) * 2011-11-25 2014-08-07 바이엘 인텔렉쳐 프로퍼티 게엠베하 2-요오도이미다졸 유도체
BR112015014822A2 (pt) * 2012-12-21 2017-07-11 Basf Se compostos de fórmula i, composição, utilização de um composto, método para o combate dos fungos nocivos e semente revestida
EP2746260A1 (en) * 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746259A1 (en) * 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
CN103694264B (zh) * 2014-01-08 2015-11-18 山东京卫制药有限公司 一种巯基氮杂环化合物及其制备方法

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048318A (en) * 1972-01-11 1977-09-13 Bayer Aktiengesellschaft 1-Substituted-1,2,4-triazole fungicides
US4147791A (en) * 1972-01-11 1979-04-03 Bayer Aktiengesellschaft 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants
US3912752A (en) * 1972-01-11 1975-10-14 Bayer Ag 1-Substituted-1,2,4-triazoles
DE2324010C3 (de) * 1973-05-12 1981-10-08 Bayer Ag, 5090 Leverkusen 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen
US4079062A (en) * 1974-11-18 1978-03-14 Janssen Pharmaceutica N.V. Triazole derivatives
ZA774497B (en) * 1976-07-29 1978-06-28 Ici Ltd Processes and compositions for combating fungi
IE45765B1 (en) * 1976-08-19 1982-11-17 Ici Ltd Triazoles and imidazoles useful as plant fungicides and growth regulating agents
US4598085A (en) * 1977-04-27 1986-07-01 Janssen Pharmaceutica N.V. Fungicidal 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles
US4654332A (en) * 1979-03-07 1987-03-31 Imperial Chemical Industries Plc Heterocyclic compounds
AU542623B2 (en) * 1980-05-16 1985-02-28 Bayer Aktiengesellschaft 1-hydroxyethyl-azole derivatives
GB2078719B (en) * 1980-06-02 1984-04-26 Ici Ltd Heterocyclic compounds
EP0052424B2 (en) * 1980-11-19 1990-02-28 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
AR228764A1 (es) * 1980-12-20 1983-04-15 Bayer Ag 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos
EP0061835B1 (en) * 1981-03-18 1989-02-01 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
US5266585A (en) * 1981-05-12 1993-11-30 Ciba-Geigy Corporation Arylphenyl ether derivatives, compositions containing these compounds and use thereof
DE3218130A1 (de) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide
PT78388B (en) * 1983-04-12 1986-09-15 Smithkline Beckman Corp Dopamine-beta-hydroxylase inhibitors
CA1227801A (en) * 1983-11-10 1987-10-06 Ted T. Fujimoto .alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES
DE3511411A1 (de) * 1985-03-29 1986-10-02 Basf Ag, 6700 Ludwigshafen Verwendung von azolylmethyloxiranen zur bekaempfung von viralen erkrankungen
IL78175A (en) * 1985-03-29 1989-10-31 Basf Ag Azolylmethyloxiranes,their preparation and their use as fungicide crop protection agents
US4719223A (en) * 1985-10-31 1988-01-12 Smithkline Beckman Corporation Imidazolethiol dopamine-beta-hydroxylase inhibitors
IT1204773B (it) * 1986-01-23 1989-03-10 Montedison Spa Azolilderivati fungicidi
US4952232A (en) * 1987-04-29 1990-08-28 E. I. Du Pont De Nemours And Company Antifungal carbinols
US5084465A (en) * 1986-06-23 1992-01-28 Du Pont Merck Pharmaceutical Company Antifungal carbinols
EP0251086B1 (en) * 1986-06-23 1993-03-17 The Du Pont Merck Pharmaceutical Company Antifungal carbinols
US4965281A (en) * 1986-06-23 1990-10-23 E. I. Du Pont De Nemours And Cmopany Antifungal carbinols
US5087635A (en) * 1986-07-02 1992-02-11 Rohm And Haas Company Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles
JPH0625140B2 (ja) * 1986-11-10 1994-04-06 呉羽化学工業株式会社 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤
DE3812967A1 (de) * 1987-06-24 1989-01-05 Bayer Ag Azolylmethyl-cyclopropyl-derivate
DE3725397A1 (de) * 1987-07-31 1989-02-09 Bayer Ag 1,4-disubstituierte 1-azolyl-3,3-dimethylbutan-derivate
US5256683A (en) * 1988-12-29 1993-10-26 Rhone-Poulenc Agrochimie Fungicidal compositions containing (benzylidene)-azolylmethylcycloalkane
MA21706A1 (fr) * 1988-12-29 1990-07-01 Rhone Poulenc Agrochimie Benzolidene azolylmethylcycloalcane et utilisation comme fongicide.
DE19528046A1 (de) * 1994-11-21 1996-05-23 Bayer Ag Triazolyl-Derivate
DE19520095A1 (de) * 1995-06-01 1996-12-05 Bayer Ag Mercapto-triazolyl-silane
DE29611968U1 (de) * 1996-07-10 1996-09-05 Krumbein, Wolfgang, 99891 Tabarz Vorrichtung zum Schneiden von Torten und ähnlichen Kuchenarten

Also Published As

Publication number Publication date
JP2000511164A (ja) 2000-08-29
AU2894997A (en) 1997-12-09
WO1997044323A1 (de) 1997-11-27
CN1226235A (zh) 1999-08-18
BR9709019A (pt) 1999-08-03
DE59709790D1 (de) 2003-05-15
EP0901472A1 (de) 1999-03-17
DE19620408A1 (de) 1997-11-27
US6114539A (en) 2000-09-05

Similar Documents

Publication Publication Date Title
EP0793657B1 (de) Mikrobizide triazolyl-derivate
EP0832083B1 (de) Mikrobizide (mercapto-triazolylmethyl)-dioxacycloalkane
EP0906292B1 (de) Triazolyl-mercaptide und ihre verwendung als mikrobizide
EP0900208B1 (de) Acylmercapto-triazolyl-derivate und ihre verwendung als mikrobizide
EP0901478B1 (de) Thiocyano-triazolyl-derivate und ihre verwendung als mikrobizide
EP0912529B1 (de) Triazolyl-disulfide
EP0828719B1 (de) Mikrobizide (mercapto-triazolylmethyl)-cyclopentanole
EP0901477B1 (de) Sulfonyl-mercapto-triazolyl-derivate und ihre verwendung als mikrobizide
EP0828734B1 (de) Triazolylmethyl-oxirane
EP0842158A1 (de) Mikrobizide 2-phenylethyl-mercapto-triazole
EP0843668A1 (de) Mikrobizide mercapto-triazolyl-ketone
EP0901472B1 (de) Mercapto-imidazolyl-derivate und ihre verwendung als mikrobizide
WO1996038424A1 (de) Cycloalkan-benzyliden microbizide
EP0843669A1 (de) Mikrobizide mercapto-triazolyl-nitrile
WO1996039395A1 (de) Mikrobizide (mercapto-triazolylmethyl)-butanole
WO1996041798A1 (de) Mikrobizide (mercapto-triazolylmethyl)-ethanole
WO1996039394A1 (de) Mercapto-bis-triazole
WO1996036634A1 (de) Oxiranyl-hydroxyethyl-triazole
DE19517719A1 (de) Phenyl-cyclopropyl-carboxy-azole
WO1996036635A1 (de) Oxiranyl-triazole

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19981221

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE DK ES FR GB IE IT LI NL

17Q First examination report despatched

Effective date: 20000728

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER CROPSCIENCE AG

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE DK ES FR GB IE IT LI NL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20030409

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20030409

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030409

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: GERMAN

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030531

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030531

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20030531

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 20030520

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20030709

NLV1 Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20031030

ET Fr: translation filed
REG Reference to a national code

Ref country code: IE

Ref legal event code: FD4D

Ref document number: 0901472E

Country of ref document: IE

BERE Be: lapsed

Owner name: *BAYER CROPSCIENCE A.G.

Effective date: 20030531

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20040112

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20040420

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20040427

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20040505

Year of fee payment: 8

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050509

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20051201

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20050509

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20060131

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20060131